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Philadelphia Phillies: Ranking 25 Greatest Offseason Moves in Team History

Greg PintoCorrespondent INovember 18, 2011

Philadelphia Phillies: Ranking 25 Greatest Offseason Moves in Team History

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    Philadelphia Phillies' fans across the globe can rejoice and be happy during this time of year. Yes, the club missed out on the ultimate goal of winning the World Series in 2011, but if it is any consolation, the days of not winning the World Series and then watching other clubs gobble up all of the winter's top free agents and making the biggest trades are over.

    The Phillies, with general manager Ruben Amaro Jr. at the helm, have become big game hunters. They're in the business of luring the game's top players to the City of Brotherly Love and partner, business is booming.

    In the last few off-seasons alone, the Phillies have brought two aces to the city (one by waiving his no-trade clause and the other, by negotiating a contract in secrecy,) inked a closer to the most lucrative reliever's contract of all-time, and convinced a Gold Glove second baseman to move to the hot-corner, and that is just to name a few.

    This wasn't always the case.

    For a franchise with more than 10,000 losses, the Phillies have certainly endured their darkest hours. They weren't always able to pull off the big trade or sign the big name free agent. So as we play witness to their better days in the present, let's look back to the past to see how far they've come, and where today's deals rank among the greatest off-season moves of all-time.

    Finally, just a reminder before we begin. Any move made during the off-season (trade, signings, etc.) is fair game for this list!

Honorable Mention

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    Philadelphia Phillies sign Cliff Lee: Through one season, it certainly looks as though the Phillies' decision to take the moniker of "mystery team" and steal Lee off of the free agent market was a good decision, but then again, it has only been one season. A lot of things can happen over the course of the remaining four seasons, and with just one season to go by, it is probably a bit too soon to seriously rank this deal. For now, it sits just outside of the top 25.

25. Phillies Sign a Pair Prior to 1993

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    The 1993 version of the Philadelphia Phillies were an interesting group of guys. With mullets and beer bellies, they were a rag-tag group of baseball players that somehow managed to put it all together and capture a National League pennant. Sure, there was talent. Led by the exploits of Lenny Dykstra, Darren Daulton, and John Kruk among others, they were talented, but a dark horse at best.

    The Phillies inked a couple of player prior to the 1993 season that would play key roles in the success of the club. The first was right fielder Jim Eisenreich, who was coming off of a down season with the Kansas City Royals and would cost the club just $675,000. Eisenreich posted an OPS of .808 for the Phils, getting most of the starts in right field.

    The Phillies also managed to sign Pete Incaviglia during the off-season for a little more than $1 million, and he would go on a complete tear at the plate. "Inky" would go on to post an OPS of .848 for the Phillies in 1993, hitting 24 home runs along the way, helping to drive the Phillies' offense.

24. Phillies Lure Jim Thome to Town

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    Jim Thome signing with the Philadelphia Phillies is at the back end of this list because it can be interpreted in one of two ways, for the most part.

    First, there is the popular school of thought that Thome's signing with the Phillies completely changed the landscape of baseball in Philadelphia. It has been said on numerous occasions that Thome playing for the Phillies opened the door for free agents and star players to come to Philly, and to some extent, that is true.

    After all, in his first season with the Phillies, Thome slugged a league-leading 47 home runs and posted an OPS of .958 as the Phils finished with a winning record of 86-76—a record that would hover in a similar position for the next few seasons before gradually climbing.

    On the other hand, you could take the pessimist's perspective. While signing Thome to that large contract was successful in the short term, it had long term ramifications. While the Phillies knew help was on the way, they weren't going to be successful for a few seasons. They wound up trading Thome to the Chicago White Sox while paying off his contract in increments over the next several seasons.

23. Phillies Acquire Manny Trillo, Greg Gross

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    Entering the 1979 season, it was obvious that the Philadelphia Phillies were just a few pieces away from a World Series title. In order to strengthen the roster in a few places, they struck a deal with the Chicago Cubs, sending Henry Mack, Derek Botelho, Barry Foote, Jerry Martin, and Ted Sizemore to the Cubbies in exchange for Manny Trillo, Greg Gross, and Dave Rader.

    Trillo was the obvious target, as the Phillies were in need of a second baseman and he fit the built. He won a Gold Glove in his first season with the club, and along with Larry Bowa, completed one of the slickest-fielding middle-infields baseball has ever seen. Trillo would anchor second base for the 1980 World Series club, winning two more Gold Gloves, two Silver Sluggers, and making two straight All-Star appearances.

    Gross may have been the secret weapon. Though he was sent to the bench, he would become the club's pinch hitter extraordinaire, so much so that Baseball-Reference has him listed, under position, as a "pinch hitter." He would become known for his timely pinch hits, as well as spot starts, and was an integral part of the World Series club.

    Rader became the forgotten man. He was traded to the Boston Red Sox before the 1980 season. Ouch.

22. Phillies Ink Jim Konstanty

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    Prior to the 1948 season, the Philadelphia Phillies obtained the contractual rights of right handed pitcher Jim Konstanty from Toronto of the International League as part of a Minor League working agreement. It was a smooth move for the Phillies franchise, because in just a few seasons, he would be with the Major League club and an invaluable asset.

    The highlight of Konstanty's career with the Phillies was undoubtedly his heroics during the 1950 season. As a reliever, he appeared in 74 games which, at the time, set a Major League record. He recorded 16 wins and saved 22 games, making him an easy choice as the 1950 MVP.

    After a long season in the bullpen, he was asked to start Game 1 of the 1950 World Series in a surprise move, and though he would lose that game, he gave up just four hits in eight innings of work.

21. Phillies Acquire Al Holland, Joe Morgan

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    The Philadelphia Phillies kicked off the 1980s in the proper fashion—by winning a World Series. Though they were aging quickly, the club still had the pieces to contend, but once again, needed to patch a few holes. A few days earlier, the Phillies had moved their second baseman, Manny Trillo, to the Cleveland Indians as part of the "five-for-one" deal that brought Von Hayes to town. A new second baseman was in order.

    So just a few days removed from one of the off-season's biggest trades, the Phillies pulled off a deal with the San Francisco Giants, landing veteran second baseman Joe Morgan and a premium reliever in Al Holland, in exchange for Charles Penigar, Mark Davis, and Mike Krukow.

    Acquiring Morgan may have been a bit of a surprise. Though he still had the talent, to most, he was past his prime, having turned 39-years-old. Though he hit just .230 for the Phillies in his lone season, he still posted an OPS of .773, thanks in large part to a phenomenal on-base percentage.

    The success that Holland had may have been the bigger surprise. In his first season, he appeared in 68 games, posting an ERA of 2.26, saving 25 games, and posting a WHIP of 1.015. He finished sixth in the league's Cy Young voting and ninth in MVP voting. Though he had similar success the next season, the role in 1983, along with Morgan, was a large part of the reason the Phillies went back to the World Series.

20. Phillies Acquire Roy Halladay

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    Entering the 2009 season, the Philadelphia Phillies had their eye on Roy Halladay, then of the Toronto Blue Jays. In desperate need of a legitimate "ace," the Phillies coveted one of baseball's best, and as the traded deadline rolled around, found themselves unable to work out a deal with the Jays, instead acquiring Cliff Lee, then of the Cleveland Indians.

    However, the Phillies wanted Halladay so bad that even with Lee under contract, they struck a deal with the Jays during the off-season, bringing Halladay to Philadelphia and sending Lee west to restock the farm system.

    Through two seasons in red-pinstripes, Halladay has been everything the Phillies could have hoped for. He's posted a record of 40-16 with an ERA of 2.40 and tossed 17 complete games. "Doc" has made two consecutive trips to the All-Star Game, and he won the Cy Young Award in 2010, finishing second in the 2011 voting.

    Sure, the Phillies may have traded three good prospects to Toronto, but they received the best in the business in Halladay.

19. Tully Sparks Joins the Phillies, Ditches the Americans

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    The MLB's off-season was not always a cool, calculated adventure. Once upon a time, especially during the early 1900s, baseball's off-season was governed by vague rules and players often decided their own fate. Frankly, it is a process not worth getting in to, but the point remains the same—it was not nearly as official a process as it is today.

    That opened the door for players to go where they wanted, and Tully Sparks took advantage of that by jumping from the Boston Americans to the Philadelphia Phillies prior to the 1903 season, and the Phils were certainly happy to have him. He would go on to win 95 games and post an ERA of 2.48 as a member of the Phillies.

18. Phillies Select Pinky Whitney in Rule 5 Draft

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    Though the specifics of MLB's Rule 5 Draft have changed over the years, the concept has remained the same. Major League teams are given the opportunity to draft players out of other organizations if they are not given the proper chance to reach that club's roster.

    The Philadelphia Phillies have taken a chance in this draft many times throughout its history, but few, if any, have been more successful than Pinky Whitney. After drafting him out of New Orleans of the Southern Association, Whitney spent the first five and a half seasons of his 10-year career with the Phillies in Philadelphia.

    Whitney was a work-horse, playing in a ton of games and doing more than a solid job. In his career with the Phillies, he posted an OPS of .789 and drove in 734 runs, receiving votes as the MVP in three of those 10 seasons.

17. Phillies Acquire Jim Bunning, Gus Triandos

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    The Philadelphia Phillies were about to make an impressive run (perhaps for the wrong reasons) during the 1964 season, and it is hard to imagine that they would have been as successful (or as unsuccessful, depending on how you look at the situation) without the contributions of Jim Bunning.

    Prior to the season, the Phillies were looking to add a reliable starter to the top of their rotation to pair with lefty Chris Short, and after a "disappointing" season with the Detroit Tigers, the Phils were able to strike a deal, landing Bunning and catcher Gus Triandos in exchange for Don Demeter and Jack Hamilton.

    Bunning would become the ace of the 1964 staff and several staffs beyond that season. In '64, he won 19 games and posted an ERA of 2.63. Overworked by Gene Mauch, he was not nearly as successful at the end of the season, and was at the forefront of the collapse simply known as the "Phold."

    He was great as a Phillie, however, winning 89 games in six seasons and posting an ERA of 2.93. The highlight of his Phillies' career was tossing a perfect game on Fathers' Day—the first in club history—which was, perhaps ironically, caught by Triandos.

16. Phillies Sign Larry Bowa

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    Major League teams sign plenty of amateur free agents over the course of each and every season, a tradition that has its roots in the era of baseball prior to free agency. Nowadays it is very rare to see a player signed as an "amateur free agent" reach the Major Leagues, and while the feat was not nearly as rare as it was in the 1960s and before, it was certainly a rarity to sign an amateur free agent that would eventually spend 12 Major League seasons with the club.

    That, however, was the case for Larry Bowa, who inked a deal with the Philadelphia Phillies as an amateur free agent and became a staple as the club's shortstop. In those 12 seasons, he posted an OPS of just .624, but played supreme defense.

    Nicknamed "Gnat" because of his ability to, well, be a pest, Bowa was sent to the All-Star Game five times and won two Gold Gloves. Of course, he was eventually dealt to the Chicago Cubs in the deal that will never be known as the trade that brought Ivan de Jesus to town, but the day the Phillies traded Ryne Sandberg.

15. Phillies Ink Curt Simmons as a Free Agent

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    Born and raised in Pennsylvania, the Philadelphia Phillies had always had the inside track on Curt Simmons. He was the starting pitcher for the high school All-Stars of Pennsylvania, who squared off with the Phillies as a promotional event, and pitched well enough to win. The Phils simply had to have him, and they signed him to a contract as an amateur free agent before the 1947 season.

    He pitched his first Major League game at the age of 18—a complete game win in which he gave up just one run. He would go on to be a staple in the Phillies' rotation and a member of the 1950 "Whiz Kids" team that captured the National League pennant. In 13 season with the Phillies he collected 115 wins, posting an ERA of 3.66.

14. Phillies Acquire Ron Reed

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    As far as the Philadelphia Phillies are concerned, Ron Reed may have defined the role of "set-up man." With Tug McGraw aboard as the team's closer, the Phillies were in the market for a guy who could join him pitching in the later innings, and found their guy in Reed. The Phillies struck a deal with the St. Louis Cardinals, acquiring Reed in exchange for Mike Anderson.

    Reed would go on to spend eight years with the Phillies, finishing 255 games, posting and ERA of 3.06 and a WHIP of 1.150. He was a member of six Phils teams that made the postseason, and most importantly, a member of that 1980 World Series team.

13. Phillies Acquire Johnny Callison

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    Gene Freese had just one, average season as a member of the Philadelphia Phillies, so how did he work his way into one of the club's most important decisions? After that one season, he was sent to the Chicago White Sox in exchange for one of the greatest Phillies' players of all-time, Johnny Callison.

    After being acquired from the White Sox, the promising young outfielder would spend 10 seasons with the Phillies, developing into one of the best players to ever wear the uniform. He hit .271 as a Phillie and posted an OPS of .795, collecting 185 home runs and 265 doubles. Callison is a three-time All-Star and finished second in MVP voting in 1964.

    I think it's safe to say the Phillies were happy with this deal.

12. Phillies Acquire Tug McGraw

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    After watching him play against them for nearly a decade, the Philadelphia Phillies decided that there was only one man who could fill their need for a closer, solidifying the back end of their bullpen. That man was, of course, none other than Tug McGraw, and the Phillies offered the Mets a package of players they couldn't refuse for the "Tugger's" services, sending Mac Scarce, John Stearns, and Del Unser to New York in exchange for McGraw, Don Hahn, and Dave Schneck.

    McGraw would go on to spend 10 years at the back end of the Phillies' bullpen, saving 94 games and finishing 313 in total. He was named to one All-Star teams as a member of the Phils, but most importantly, nailed down the final out of the 1980 World Series. 

11. Phillies Purchase Rights to Billy Hamilton

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    After two seasons with the Kansas City Cowboys, Billy Hamilton's chances of making the Hall of Fame weren't very good. His fortunes may have changed for the better prior to the 1890 season, when the Philadelphia Phillies purchased his contract from the Cowboys for somewhere between $5,000 and $6,000 and his career took off.

    Hamilton would spend six seasons as a member of the Phillies, throwing up some numbers worthy of a double-take. He led the league in a bevy of statistics with the Phils, posting an OPS of .927 in total and batting .360. He stole 510 bases and drew 553 walks. He recorded 126 doubles, 51 triples, and 23 home runs—in six seasons! 

    Well worth the steep price in 1890.

10. Phillies Purchase Rights to Sam Thompson

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    Sam Thompson is one of just a few Hall of Fame players on this list, in a crude sense giving us an idea of the truly unpredictable nature of baseball's off-season. After all, I'm sure that had the Detroit Wolverines glared into their crystal ball and saw his future, they would have never sold Thompson's rights to the Philadelphia Quakers, but that is exactly what happened.

    Thompson would go onto spend 10 seasons as a member of the Quakers / Phillies, also posting ludicrous numbers. He hit .334 and posted an OPS of .89, stole 192 bases, and hit 95 home runs. He hit .415 in 1894 and drove in more than 160 runs twice.

9. Phillies Sign Del Ennis as Free Agent

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    Born and raised in Philadelphia, Pennsylvania, signing Del Ennis almost made too much sense for the Philadelphia Phillies. Coming out of high school, he was a big, athletic kid with something to prove at the Major League level, giving him the ambition and drive to be a big league hitter, and before Mike Schmidt and Ryan Howard came around years later, he was the preeminent slugger of the Phillies' franchise.

    He made his debut in 1946 at just 21 years of age, and in total, would go on to spend 11 seasons as a member of the Phillies. He hit 259 home runs in his Phillies career and led the league in RBI during the 1950 season, helping to lead the Phillies to the National League pennant. A three-time All-Star, Ennis would receive votes for the MVP Award in seven different seasons as a Phillie.

8. Phillies Acquire Bobby Abreu

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    Any time you can swap a shortstop known simply because of his borderline defensive abilities for even a little bit of offensive production, you've probably made a good trade. Any time you can swap said "defensive" shortstop for a five-tool outfielder that has since posted fringe Hall of Fame type numbers, you've made a great deal.

    That was the case back in 1997, when the Philadelphia Phillies traded their "defensively adept" shortstop, Kevin Stocker, to the Tampa Bay Devil Rays in exchange for outfielder Bobby Abreu. Abreu would go on to be one of the Phillies' lone bright spots during the late 1990s and early 2000s, hitting .303 with a .928 OPS. He also swiped 254 bases and hit 195 home runs.

    He will forever be questioned about his character, but there is certainly no questioning his talent on the field, effectively making him one of the greatest Phillies of all-time.

7. Phillies Sign Dick Allen as Amateur Free Agent

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    Speaking of players who will never be truly appreciated for just how talented they were, that brings us to Dick Allen.

    The Philadelphia Phillies agreed to sign the "Wampum Walloper" out of high  school before the 1960 season, sending him to the Minor Leagues for a bit of seasoning before making him the starting third baseman for the 1964 season. Needless to say, his rookie year was inspiring. He helped propel the Phillies offense before their historic collapse (yes, the "Phold" once again) and captured the Rookie of the Year Award.

    He would spend seven seasons with the Phillies after inking his first contract, returning to Philadelphia for two more seasons later in his career. He hit .290 as a member of the Phils, hitting 204 home runs and the same amount of doubles. He posted an OPS of .902 and led the league in a bevy of statistics, later winning an MVP award with the Chicago White Sox.

6. Phillies Acquire Cy Williams

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    When the Philadelphia Phillies traded Dode Paskert to the Chicago Cubs, they were moving a talented offensive player in his own right. So when they received Cy Williams, he had relatively large shoes to fill. After a couple of solid seasons with the Cubs, the Phillies probably weren't aware of the level of talent they were getting.

    Williams would go on to spend 13 seasons as a member of the Phillies, batting .306 and posting an OPS of .880. He slugged 217 home runs, drove in 795 runs, drew 551 walks, and in total, collected 1,553 hits.

    Safe to say, those shoes didn't fit very comfortably by the time Williams' career with the Phillies had ended.

5. Phillies Ink Richie Ashburn to a Contract

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    When the Philadelphia Phillies signed Richie Ashburn as an amateur free agent prior to the 1945 season, they weren't just signing a future All-Star, but a future legend. He spent 12 seasons on the field for the Phillies, collecting 1,114 hits en route to a .311 career batting average for the Phils and .782 OPS. Ashburn had 287 doubles to his credit, and added 97 triples.

    Of course, when he was finished on the field, "Whitey" transitioned flawlessly into the broadcast booth, creating endless memorable moments with his good friend Harry Kalas, becoming a Philadelphia icon in the process.

4. Phillies Sign Robin Roberts as an Amateur Free Agent

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    The Philadelphia Phillies signed big right handed starter Robin Roberts as an amateur free agent prior to the 1948 season, and unlike most amateur free agents of the day, he was sent straight to Philadelphia to help out the big league club at just 21 years old.

    A few seasons later, he would lead the Phils' pitching staff to the National League pennant, beginning one of the most dominant periods of pitching of all time. Roberts would roll off seven straight All-Star appearances, recording MVP votes in each of those seasons, and came one win away during the 1956 season of pitching seven straight seasons with at least 20 wins.

    In total he would spend 14 seasons as a member of the Phillies, winning 234 games and posting an ERA of 3.46. A Hall of Famer, it goes without saying that signing Roberts was one of the greatest transactions of all-time.

3. Phillies Acquire Brad Lidge, Eric Bruntlett

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    How about a little controversy for the number three spot?

    With all of those Hall of Fame players beneath him on this list, how could Brad Lidge possibly be regarded as one of the greatest acquisitions of all time? After all, Lidge wasn't exactly great throughout the course of his Philadelphia Phillies career. But let us take a step back for a second.

    When the Phillies sent Michael Bourn, Mike Constanzo, and Geoff Geary to the Houston Astros in exchange for Lidge and Eric Bruntlett, the closer had just a year remaining on his contract. Though he would have his deal extended mid-season, in order for the deal to originally pan out, he would need to have one heck of a season.

    Boy, did he.

    Lidge converted each an every save opportunity during the regular season in 2008, collecting 41 saves before converting the next seven during the postseason as well. He posted an ERA of 1.95 on the season. Lidge would finish fourth in the Cy Young voting and eighth in MVP voting.

    Bruntlett? Well, he did score a go-ahead run in the World Series and hit a home run.

    The real question becomes this: Had the Phillies not made that trade, would they have won the World Series in 2008? I'm not so sure.

2. Phillies Select Pete Alexander in the Rule 5 Draft

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    As was stated earlier in the slide show, the Rule 5 Draft was a much different even back in 1910 than it is in present day, but the thought process remains the same. The Philadelphia Phillies selected Pete Alexander from Syracuse of the New York State league in the draft, sending him to Philadelphia to join their rotation.

    Good decision.

    Alexander would go on to spend eight seasons as a member of the Phillies, collecting 190 wins and posting an ERA of just 2.18. He recorded MVP votes in three different seasons, recorded three seasons with at least 30 wins, and ultimately, was inducted into the Hall of Fame.

1. Phillies Acquire Steve Carlton

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    Speaking of Hall of Famers, how about that Steve Carlton guy?

    When the Philadelphia Phillies couldn't come to an agreement on a new contract for staff ace Rick Wise, they put him on the trade block to see who would bite. As it turns out, the St. Louis Cardinals had an unhappy pitcher of their own in Carlton, and management was so upset about his contract situation that they wanted him gone. The teams swapped pitchers and in hindsight, I think it is safe to say the Phillies got the better end of the deal.

    Carlton would go on to spend 15 seasons with the Phillies, picking up 241 wins to the tune of a 3.09 ERA. He pitched on two World Series clubs, including the 1980 championship group, and four other postseasons. "Lefty" would capture an incredible four Cy Young Awards with the Phillies, making seven All-Star appearances as well.

    Needless to say, this was the Phillies' greatest off-season move of all-time—and more simply put—the greatest transaction of all-time, period.

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